#------------------------------------------------------------------------------
#$Date: 2017-03-02 00:31:50 +0200 (Thu, 02 Mar 2017) $
#$Revision: 192660 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/00/02/8000235.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8000235
loop_
_publ_author_name
'Austin, Ashli'
'Hestand, Nicholas J.'
'McKendry, Ian G.'
'Zhong, Chuwei'
'Zhu, Xuanyu'
'Zdilla, Michael J.'
'Spano, Frank C.'
'Szarko, Jodi M.'
_publ_section_title
;
 Enhanced Davydov Splitting in Crystals of a Perylene Diimide Derivative.
;
_journal_name_full               'The journal of physical chemistry letters'
_journal_page_first              1118
_journal_page_last               1123
_journal_paper_doi               10.1021/acs.jpclett.7b00283
_journal_year                    2017
_chemical_formula_moiety         '0.25(C34 H28 N2 O4), 0.75(C34 H30 N2 O4)'
_chemical_formula_sum            'C34 H29.5 N2 O4'
_chemical_formula_weight         530.09
_chemical_name_common            'B2 perylene diimide'
_chemical_name_systematic
;
2,9-di(pentan-3-yl)anthra[2,1,9-def:6,5,10-d'e'f']diisoquinoline-
1,3,8,10(2H,9H)-tetraone
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.329(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.897(6)
_cell_length_b                   7.3290(10)
_cell_length_c                   21.104(4)
_cell_measurement_reflns_used    3094
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.70
_cell_measurement_theta_min      2.16
_cell_volume                     5157.9(15)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (Bruker AXS)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.97
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.581
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0858
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.581
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            43769
_diffrn_reflns_point_group_measured_fraction_full 0.581
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         20.847
_diffrn_reflns_theta_min         1.221
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0765 before and 0.0672 after correction.
The Ratio of minimum to maximum transmission is 0.8497.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       needle
_exptl_crystal_F_000             2236
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     738
_refine_ls_number_reflns         5427
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0798P)²+3.4285P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1524
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3861
_reflns_number_total             5427
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jz7b00283_si_001.cif
_cod_data_source_block           solve_14_a
_cod_original_cell_volume        5157.9(14)
_cod_original_formula_sum        'C34 H29.50 N2 O4'
_cod_database_code               8000235
_shelxl_version_number           2014/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.940
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Rigid bond restraints
 C67, C67A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C67 \\sim C67A: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
4. Others
 Sof(H68D)=Sof(H68E)=Sof(H68F)=Sof(C67A)=Sof(H67C)=Sof(H67D)=1-FVAR(1)
 Sof(C67)=Sof(H67A)=Sof(H67B)=Sof(H68A)=Sof(H68B)=Sof(H68C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C13(H13), C30(H30), C47(H47)
5.b Secondary CH2 refined with riding coordinates:
 C65(H65A,H65B), C67(H67A,H67B), C67A(H67C,H67D), C14(H14A,H14B), C16(H16A,
 H16B), C31(H31A,H31B), C33(H33A,H33B), C48(H48A,H48B), C50(H50A,H50B)
5.c Me refined with riding coordinates:
 C68(H68A,H68B,H68C), C68(H68D,H68E,H68F)
5.d Aromatic/amide H refined with riding coordinates:
 C54(H54), C55(H55), C60(H60), C61(H61), C3(H3), C4(H4), C9(H9), C10(H10),
 C20(H20), C21(H21), C26(H26), C27(H27), C37(H37), C38(H38), C43(H43), C44(H44)
5.e Idealised Me refined as rotating group:
 C66(H66A,H66B,H66C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C32(H32A,H32B,
 H32C), C34(H34A,H34B,H34C), C49(H49A,H49B,H49C), C51(H51A,H51B,H51C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O7 O 0.15200(10) 0.1754(4) 0.15862(16) 0.0526(9) Uani 1 1 d . . . . .
O8 O 0.05644(10) 0.2851(4) 0.28114(17) 0.0563(10) Uani 1 1 d . . . . .
N4 N 0.10603(11) 0.2427(5) 0.22237(19) 0.0401(10) Uani 1 1 d . . . . .
C52 C 0.06708(15) 0.2933(6) 0.2285(2) 0.0405(13) Uani 1 1 d . . . . .
C53 C 0.03933(14) 0.3556(6) 0.1704(2) 0.0363(12) Uani 1 1 d . . . . .
C54 C 0.00105(14) 0.4083(6) 0.1743(2) 0.0390(12) Uani 1 1 d . . . . .
H54 H -0.0078 0.4013 0.2145 0.047 Uiso 1 1 calc R . . . .
C55 C -0.02515(14) 0.4720(6) 0.1204(2) 0.0373(12) Uani 1 1 d . . . . .
H55 H -0.0515 0.5075 0.1246 0.045 Uiso 1 1 calc R . . . .
C56 C -0.01359(13) 0.4850(5) 0.0606(2) 0.0309(11) Uani 1 1 d . . . . .
C57 C 0.02628(13) 0.4319(5) 0.0555(2) 0.0299(11) Uani 1 1 d . . . . .
C58 C 0.05251(13) 0.3656(5) 0.1112(2) 0.0304(11) Uani 1 1 d . . . . .
C59 C 0.04055(12) 0.4462(5) -0.0037(2) 0.0280(11) Uani 1 1 d . . . . .
C60 C 0.07960(13) 0.3907(5) -0.0054(2) 0.0328(11) Uani 1 1 d . . . . .
H60 H 0.0894 0.4007 -0.0447 0.039 Uiso 1 1 calc R . . . .
C61 C 0.10476(14) 0.3212(6) 0.0484(2) 0.0360(12) Uani 1 1 d . . . . .
H61 H 0.1310 0.2812 0.0451 0.043 Uiso 1 1 calc R . . . .
C62 C 0.09177(13) 0.3101(5) 0.1061(2) 0.0327(12) Uani 1 1 d . . . . .
C63 C 0.11882(15) 0.2379(6) 0.1633(2) 0.0376(12) Uani 1 1 d . . . . .
C64 C 0.13502(15) 0.1907(7) 0.2816(3) 0.0556(16) Uani 1 1 d . . . . .
C65 C 0.1310(2) -0.0033(9) 0.2976(3) 0.095(2) Uani 1 1 d . . . . .
H65A H 0.1028 -0.0213 0.3030 0.114 Uiso 1 1 calc R . . . .
H65B H 0.1345 -0.0739 0.2590 0.114 Uiso 1 1 calc R . . . .
C66 C 0.15504(19) -0.0873(10) 0.3503(3) 0.095(2) Uani 1 1 d . . . . .
H66A H 0.1831 -0.0840 0.3446 0.143 Uiso 1 1 calc GR . . . .
H66B H 0.1466 -0.2144 0.3532 0.143 Uiso 1 1 calc GR . . . .
H66C H 0.1523 -0.0224 0.3898 0.143 Uiso 1 1 calc GR . . . .
C67 C 0.1465(5) 0.336(2) 0.3210(7) 0.084(4) Uani 0.449(10) 1 d . U P A 1
H67A H 0.1298 0.3307 0.3550 0.100 Uiso 0.449(10) 1 calc R . P A 1
H67B H 0.1378 0.4461 0.2951 0.100 Uiso 0.449(10) 1 calc R . P A 1
C68 C 0.1865(2) 0.3721(10) 0.3534(5) 0.134(4) Uani 1 1 d . . . . .
H68A H 0.1868 0.4843 0.3787 0.202 Uiso 0.449(10) 1 calc R . P A 1
H68B H 0.1960 0.2700 0.3821 0.202 Uiso 0.449(10) 1 calc R . P A 1
H68C H 0.2041 0.3866 0.3216 0.202 Uiso 0.449(10) 1 calc R . P A 1
H68D H 0.2109 0.4430 0.3521 0.202 Uiso 0.551(10) 1 calc R . P A 2
H68E H 0.1663 0.4509 0.3671 0.202 Uiso 0.551(10) 1 calc R . P A 2
H68F H 0.1928 0.2710 0.3839 0.202 Uiso 0.551(10) 1 calc R . P A 2
C67A C 0.1720(4) 0.3044(17) 0.2937(6) 0.083(4) Uani 0.551(10) 1 d . U P A 2
H67C H 0.1937 0.2310 0.2806 0.100 Uiso 0.551(10) 1 calc R . P A 2
H67D H 0.1673 0.4097 0.2639 0.100 Uiso 0.551(10) 1 calc R . P A 2
O1 O 0.34746(8) 0.1422(3) 0.35665(12) 0.0237(7) Uani 1 1 d . . . . .
O2 O 0.43548(7) 0.2641(4) 0.22286(13) 0.0266(7) Uani 1 1 d . . . . .
N1 N 0.38888(9) 0.2180(4) 0.28702(14) 0.0180(8) Uani 1 1 d . . . . .
C1 C 0.37868(12) 0.2131(5) 0.34839(19) 0.0195(10) Uani 1 1 d . . . . .
C2 C 0.40698(10) 0.2953(5) 0.40239(18) 0.0146(9) Uani 1 1 d . . . . .
C3 C 0.39601(11) 0.3099(5) 0.46165(19) 0.0180(10) Uani 1 1 d . . . . .
H3 H 0.3702 0.2690 0.4672 0.022 Uiso 1 1 calc R . . . .
C4 C 0.42212(11) 0.3837(5) 0.51378(19) 0.0183(10) Uani 1 1 d . . . . .
H4 H 0.4136 0.3951 0.5541 0.022 Uiso 1 1 calc R . . . .
C5 C 0.46042(10) 0.4413(5) 0.50805(18) 0.0146(9) Uani 1 1 d . . . . .
C6 C 0.47251(10) 0.4268(5) 0.44702(18) 0.0151(9) Uani 1 1 d . . . . .
C7 C 0.44498(10) 0.3557(5) 0.39392(18) 0.0155(9) Uani 1 1 d . . . . .
C8 C 0.51110(10) 0.4862(5) 0.43705(17) 0.0142(9) Uani 1 1 d . . . . .
C9 C 0.51996(11) 0.4761(5) 0.37541(19) 0.0199(10) Uani 1 1 d . . . . .
H9 H 0.5454 0.5175 0.3682 0.024 Uiso 1 1 calc R . . . .
C10 C 0.49247(11) 0.4066(5) 0.32354(18) 0.0201(10) Uani 1 1 d . . . . .
H10 H 0.4995 0.4019 0.2820 0.024 Uiso 1 1 calc R . . . .
C11 C 0.45544(10) 0.3452(5) 0.33189(18) 0.0151(9) Uani 1 1 d . . . . .
C12 C 0.42654(11) 0.2740(5) 0.2766(2) 0.0196(10) Uani 1 1 d . . . . .
C13 C 0.35875(11) 0.1536(5) 0.22989(18) 0.0208(10) Uani 1 1 d . . . . .
H13 H 0.3692 0.1905 0.1904 0.025 Uiso 1 1 calc R . . . .
C14 C 0.31780(11) 0.2471(5) 0.2263(2) 0.0257(10) Uani 1 1 d . . . . .
H14A H 0.3004 0.2127 0.1852 0.031 Uiso 1 1 calc R . . . .
H14B H 0.3051 0.2003 0.2618 0.031 Uiso 1 1 calc R . . . .
C15 C 0.31975(12) 0.4544(5) 0.2307(2) 0.0311(11) Uani 1 1 d . . . . .
H15A H 0.3333 0.5022 0.1969 0.047 Uiso 1 1 calc GR . . . .
H15B H 0.3347 0.4903 0.2730 0.047 Uiso 1 1 calc GR . . . .
H15C H 0.2925 0.5040 0.2250 0.047 Uiso 1 1 calc GR . . . .
C16 C 0.35569(11) -0.0539(5) 0.2288(2) 0.0251(10) Uani 1 1 d . . . . .
H16A H 0.3508 -0.0967 0.2712 0.030 Uiso 1 1 calc R . . . .
H16B H 0.3324 -0.0905 0.1959 0.030 Uiso 1 1 calc R . . . .
C17 C 0.39311(12) -0.1472(5) 0.2140(2) 0.0287(11) Uani 1 1 d . . . . .
H17A H 0.3967 -0.1152 0.1703 0.043 Uiso 1 1 calc GR . . . .
H17B H 0.3902 -0.2797 0.2173 0.043 Uiso 1 1 calc GR . . . .
H17C H 0.4166 -0.1066 0.2450 0.043 Uiso 1 1 calc GR . . . .
O3 O 0.33772(8) 0.8825(4) 0.58100(14) 0.0310(7) Uani 1 1 d . . . . .
O4 O 0.34030(8) 0.6529(4) 0.38055(13) 0.0259(7) Uani 1 1 d . . . . .
N2 N 0.33737(9) 0.7677(4) 0.47998(15) 0.0197(8) Uani 1 1 d . . . . .
C18 C 0.35604(11) 0.8533(5) 0.5371(2) 0.0206(10) Uani 1 1 d . . . . .
C19 C 0.39885(10) 0.9029(5) 0.54301(18) 0.0158(9) Uani 1 1 d . . . . .
C20 C 0.41907(11) 0.9769(5) 0.59915(19) 0.0203(10) Uani 1 1 d . . . . .
H20 H 0.4055 0.9931 0.6344 0.024 Uiso 1 1 calc R . . . .
C21 C 0.45918(11) 1.0291(5) 0.60565(19) 0.0194(10) Uani 1 1 d . . . . .
H21 H 0.4726 1.0762 0.6457 0.023 Uiso 1 1 calc R . . . .
C22 C 0.47989(11) 1.0136(5) 0.55483(18) 0.0145(9) Uani 1 1 d . . . . .
C23 C 0.45959(10) 0.9397(5) 0.49536(18) 0.0153(9) Uani 1 1 d . . . . .
C24 C 0.41897(11) 0.8809(5) 0.49052(18) 0.0150(9) Uani 1 1 d . . . . .
C25 C 0.47832(10) 0.9254(5) 0.44029(17) 0.0135(9) Uani 1 1 d . . . . .
C26 C 0.45667(10) 0.8508(5) 0.38399(18) 0.0155(9) Uani 1 1 d . . . . .
H26 H 0.4689 0.8420 0.3470 0.019 Uiso 1 1 calc R . . . .
C27 C 0.41749(11) 0.7887(5) 0.38063(18) 0.0178(10) Uani 1 1 d . . . . .
H27 H 0.4037 0.7358 0.3418 0.021 Uiso 1 1 calc R . . . .
C28 C 0.39863(11) 0.8032(5) 0.43292(18) 0.0168(10) Uani 1 1 d . . . . .
C29 C 0.35688(11) 0.7353(5) 0.4283(2) 0.0183(10) Uani 1 1 d . . . . .
C30 C 0.29488(11) 0.7050(5) 0.47596(19) 0.0237(10) Uani 1 1 d . . . . .
H30 H 0.2858 0.7537 0.5152 0.028 Uiso 1 1 calc R . . . .
C31 C 0.29247(11) 0.4986(5) 0.48023(19) 0.0247(10) Uani 1 1 d . . . . .
H31A H 0.3038 0.4440 0.4445 0.030 Uiso 1 1 calc R . . . .
H31B H 0.2639 0.4620 0.4747 0.030 Uiso 1 1 calc R . . . .
C32 C 0.31486(11) 0.4225(6) 0.54401(19) 0.0281(11) Uani 1 1 d . . . . .
H32A H 0.3137 0.2889 0.5429 0.042 Uiso 1 1 calc GR . . . .
H32B H 0.3023 0.4675 0.5794 0.042 Uiso 1 1 calc GR . . . .
H32C H 0.3429 0.4623 0.5507 0.042 Uiso 1 1 calc GR . . . .
C33 C 0.26649(11) 0.7852(6) 0.4183(2) 0.0305(11) Uani 1 1 d . . . . .
H33A H 0.2386 0.7509 0.4213 0.037 Uiso 1 1 calc R . . . .
H33B H 0.2727 0.7306 0.3783 0.037 Uiso 1 1 calc R . . . .
C34 C 0.26909(12) 0.9926(6) 0.4136(2) 0.0430(13) Uani 1 1 d . . . . .
H34A H 0.2494 1.0357 0.3768 0.064 Uiso 1 1 calc GR . . . .
H34B H 0.2961 1.0274 0.4077 0.064 Uiso 1 1 calc GR . . . .
H34C H 0.2634 1.0479 0.4533 0.064 Uiso 1 1 calc GR . . . .
O5 O 0.17641(8) 0.8489(4) -0.00455(14) 0.0354(8) Uani 1 1 d . . . . .
O6 O 0.13998(8) 0.6537(4) 0.18222(14) 0.0286(7) Uani 1 1 d . . . . .
N3 N 0.15844(9) 0.7352(4) 0.08690(16) 0.0231(8) Uani 1 1 d . . . . .
C35 C 0.13139(11) 0.7270(5) 0.1297(2) 0.0223(10) Uani 1 1 d . . . . .
C36 C 0.09100(11) 0.8086(5) 0.10800(19) 0.0211(10) Uani 1 1 d . . . . .
C37 C 0.06393(11) 0.8107(5) 0.14937(19) 0.0223(10) Uani 1 1 d . . . . .
H37 H 0.0717 0.7671 0.1922 0.027 Uiso 1 1 calc R . . . .
C38 C 0.02498(11) 0.8767(5) 0.12860(19) 0.0210(10) Uani 1 1 d . . . . .
H38 H 0.0068 0.8790 0.1580 0.025 Uiso 1 1 calc R . . . .
C39 C 0.01226(11) 0.9389(5) 0.06626(19) 0.0212(10) Uani 1 1 d . . . . .
C40 C 0.03986(11) 0.9365(5) 0.02265(18) 0.0175(10) Uani 1 1 d . . . . .
C41 C 0.07977(11) 0.8737(5) 0.04487(19) 0.0199(10) Uani 1 1 d . . . . .
C42 C 0.02902(11) 0.9958(5) -0.04271(19) 0.0205(10) Uani 1 1 d . . . . .
C43 C 0.05761(11) 0.9927(5) -0.0824(2) 0.0237(10) Uani 1 1 d . . . . .
H43 H 0.0503 1.0287 -0.1262 0.028 Uiso 1 1 calc R . . . .
C44 C 0.09692(12) 0.9376(5) -0.0591(2) 0.0284(11) Uani 1 1 d . . . . .
H44 H 0.1162 0.9407 -0.0867 0.034 Uiso 1 1 calc R . . . .
C45 C 0.10813(11) 0.8788(5) 0.0034(2) 0.0217(10) Uani 1 1 d . . . . .
C46 C 0.15021(12) 0.8233(5) 0.0275(2) 0.0246(10) Uani 1 1 d . . . . .
C47 C 0.19812(11) 0.6407(6) 0.1061(2) 0.0280(11) Uani 1 1 d . . . . .
H47 H 0.1957 0.5614 0.1437 0.034 Uiso 1 1 calc R . . . .
C48 C 0.23193(12) 0.7757(6) 0.1294(2) 0.0359(12) Uani 1 1 d . . . . .
H48A H 0.2579 0.7110 0.1332 0.043 Uiso 1 1 calc R . . . .
H48B H 0.2314 0.8725 0.0966 0.043 Uiso 1 1 calc R . . . .
C49 C 0.22959(13) 0.8643(6) 0.1935(2) 0.0448(13) Uani 1 1 d . . . . .
H49A H 0.2042 0.9309 0.1901 0.067 Uiso 1 1 calc GR . . . .
H49B H 0.2520 0.9492 0.2052 0.067 Uiso 1 1 calc GR . . . .
H49C H 0.2310 0.7699 0.2268 0.067 Uiso 1 1 calc GR . . . .
C50 C 0.20658(12) 0.5129(6) 0.0524(2) 0.0328(11) Uani 1 1 d . . . . .
H50A H 0.1809 0.4691 0.0272 0.039 Uiso 1 1 calc R . . . .
H50B H 0.2208 0.5813 0.0229 0.039 Uiso 1 1 calc R . . . .
C51 C 0.23181(14) 0.3502(6) 0.0798(2) 0.0458(13) Uani 1 1 d . . . . .
H51A H 0.2361 0.2697 0.0446 0.069 Uiso 1 1 calc GR . . . .
H51B H 0.2178 0.2830 0.1093 0.069 Uiso 1 1 calc GR . . . .
H51C H 0.2578 0.3930 0.1032 0.069 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C52 N4 C64 118.7(4) .
C63 N4 C52 122.6(4) .
C63 N4 C64 118.6(4) .
O8 C52 N4 120.3(5) .
O8 C52 C53 121.2(5) .
N4 C52 C53 118.5(4) .
C54 C53 C52 120.5(4) .
C54 C53 C58 119.7(4) .
C58 C53 C52 119.8(4) .
C53 C54 H54 119.4 .
C53 C54 C55 121.2(4) .
C55 C54 H54 119.4 .
C54 C55 H55 119.3 .
C56 C55 C54 121.5(4) .
C56 C55 H55 119.3 .
C55 C56 C57 118.3(4) .
C55 C56 C59 122.2(4) 3_565
C57 C56 C59 119.5(4) 3_565
C58 C57 C56 119.3(4) .
C59 C57 C56 121.4(4) .
C59 C57 C58 119.3(4) .
C53 C58 C57 120.1(4) .
C53 C58 C62 120.5(4) .
C62 C58 C57 119.4(4) .
C57 C59 C56 119.1(4) 3_565
C60 C59 C56 122.5(4) 3_565
C60 C59 C57 118.4(4) .
C59 C60 H60 118.9 .
C61 C60 C59 122.3(4) .
C61 C60 H60 118.9 .
C60 C61 H61 120.0 .
C62 C61 C60 120.0(4) .
C62 C61 H61 120.0 .
C58 C62 C63 119.7(4) .
C61 C62 C58 120.5(4) .
C61 C62 C63 119.8(4) .
O7 C63 N4 121.1(4) .
O7 C63 C62 120.5(5) .
N4 C63 C62 118.4(4) .
C65 C64 N4 111.3(4) .
C65 C64 C67A 127.6(7) .
C67 C64 N4 112.6(7) .
C67 C64 C65 129.9(8) .
C67A C64 N4 114.1(6) .
C64 C65 H65A 106.6 .
C64 C65 H65B 106.6 .
H65A C65 H65B 106.6 .
C66 C65 C64 122.9(6) .
C66 C65 H65A 106.6 .
C66 C65 H65B 106.6 .
C65 C66 H66A 109.5 .
C65 C66 H66B 109.5 .
C65 C66 H66C 109.5 .
H66A C66 H66B 109.5 .
H66A C66 H66C 109.5 .
H66B C66 H66C 109.5 .
C64 C67 H67A 106.0 .
C64 C67 H67B 106.0 .
C64 C67 C68 125.3(13) .
H67A C67 H67B 106.3 .
C68 C67 H67A 106.0 .
C68 C67 H67B 106.0 .
C67 C68 H68A 109.5 .
C67 C68 H68B 109.5 .
C67 C68 H68C 109.5 .
H68A C68 H68B 109.5 .
H68A C68 H68C 109.5 .
H68B C68 H68C 109.5 .
H68D C68 H68E 109.5 .
H68D C68 H68F 109.5 .
H68E C68 H68F 109.5 .
C67A C68 H68D 109.5 .
C67A C68 H68E 109.5 .
C67A C68 H68F 109.5 .
C64 C67A H67C 107.1 .
C64 C67A H67D 107.1 .
C68 C67A C64 121.1(12) .
C68 C67A H67C 107.1 .
C68 C67A H67D 107.1 .
H67C C67A H67D 106.8 .
C1 N1 C13 119.2(3) .
C12 N1 C1 122.5(3) .
C12 N1 C13 118.3(3) .
O1 C1 N1 120.5(3) .
O1 C1 C2 121.5(4) .
N1 C1 C2 117.9(3) .
C3 C2 C1 119.3(3) .
C3 C2 C7 119.8(3) .
C7 C2 C1 120.9(3) .
C2 C3 H3 119.6 .
C2 C3 C4 120.9(3) .
C4 C3 H3 119.6 .
C3 C4 H4 119.3 .
C5 C4 C3 121.4(4) .
C5 C4 H4 119.3 .
C4 C5 C6 118.7(3) .
C4 C5 C8 122.2(3) 3_666
C6 C5 C8 119.1(3) 3_666
C5 C6 C8 122.0(3) .
C7 C6 C5 119.0(3) .
C7 C6 C8 118.9(3) .
C2 C7 C6 120.2(3) .
C2 C7 C11 119.2(3) .
C11 C7 C6 120.7(3) .
C6 C8 C5 118.9(3) 3_666
C9 C8 C5 122.5(3) 3_666
C9 C8 C6 118.6(3) .
C8 C9 H9 119.1 .
C8 C9 C10 121.8(3) .
C10 C9 H9 119.1 .
C9 C10 H10 119.5 .
C11 C10 C9 120.9(4) .
C11 C10 H10 119.5 .
C7 C11 C12 120.5(3) .
C10 C11 C7 119.1(3) .
C10 C11 C12 120.4(3) .
O2 C12 N1 120.8(3) .
O2 C12 C11 120.8(3) .
N1 C12 C11 118.4(4) .
N1 C13 H13 106.9 .
N1 C13 C14 112.0(3) .
N1 C13 C16 111.0(3) .
C14 C13 H13 106.9 .
C16 C13 H13 106.9 .
C16 C13 C14 112.7(3) .
C13 C14 H14A 108.7 .
C13 C14 H14B 108.7 .
H14A C14 H14B 107.6 .
C15 C14 C13 114.4(3) .
C15 C14 H14A 108.7 .
C15 C14 H14B 108.7 .
C14 C15 H15A 109.5 .
C14 C15 H15B 109.5 .
C14 C15 H15C 109.5 .
H15A C15 H15B 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
C13 C16 H16A 108.9 .
C13 C16 H16B 108.9 .
H16A C16 H16B 107.7 .
C17 C16 C13 113.2(3) .
C17 C16 H16A 108.9 .
C17 C16 H16B 108.9 .
C16 C17 H17A 109.5 .
C16 C17 H17B 109.5 .
C16 C17 H17C 109.5 .
H17A C17 H17B 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
C18 N2 C30 117.8(3) .
C29 N2 C18 122.9(3) .
C29 N2 C30 119.3(3) .
O3 C18 N2 121.1(3) .
O3 C18 C19 121.1(4) .
N2 C18 C19 117.8(4) .
C20 C19 C18 120.1(3) .
C20 C19 C24 119.2(3) .
C24 C19 C18 120.7(3) .
C19 C20 H20 119.3 .
C19 C20 C21 121.4(4) .
C21 C20 H20 119.3 .
C20 C21 H21 119.3 .
C22 C21 C20 121.4(4) .
C22 C21 H21 119.3 .
C21 C22 C23 118.7(3) .
C21 C22 C25 122.4(3) 3_676
C23 C22 C25 118.9(3) 3_676
C22 C23 C24 119.0(3) .
C25 C23 C22 122.1(3) .
C25 C23 C24 119.0(3) .
C19 C24 C23 120.3(3) .
C28 C24 C19 119.6(3) .
C28 C24 C23 120.0(3) .
C23 C25 C22 119.0(3) 3_676
C26 C25 C22 122.2(3) 3_676
C26 C25 C23 118.8(3) .
C25 C26 H26 119.2 .
C25 C26 C27 121.6(3) .
C27 C26 H26 119.2 .
C26 C27 H27 119.7 .
C28 C27 C26 120.7(3) .
C28 C27 H27 119.7 .
C24 C28 C29 120.4(4) .
C27 C28 C24 119.9(3) .
C27 C28 C29 119.7(3) .
O4 C29 N2 121.1(3) .
O4 C29 C28 120.7(4) .
N2 C29 C28 118.1(3) .
N2 C30 H30 106.2 .
N2 C30 C31 111.3(3) .
N2 C30 C33 112.9(3) .
C31 C30 H30 106.2 .
C31 C30 C33 113.4(3) .
C33 C30 H30 106.2 .
C30 C31 H31A 109.0 .
C30 C31 H31B 109.0 .
C30 C31 C32 113.1(3) .
H31A C31 H31B 107.8 .
C32 C31 H31A 109.0 .
C32 C31 H31B 109.0 .
C31 C32 H32A 109.5 .
C31 C32 H32B 109.5 .
C31 C32 H32C 109.5 .
H32A C32 H32B 109.5 .
H32A C32 H32C 109.5 .
H32B C32 H32C 109.5 .
C30 C33 H33A 108.9 .
C30 C33 H33B 108.9 .
C30 C33 C34 113.5(3) .
H33A C33 H33B 107.7 .
C34 C33 H33A 108.9 .
C34 C33 H33B 108.9 .
C33 C34 H34A 109.5 .
C33 C34 H34B 109.5 .
C33 C34 H34C 109.5 .
H34A C34 H34B 109.5 .
H34A C34 H34C 109.5 .
H34B C34 H34C 109.5 .
C35 N3 C47 117.7(3) .
C46 N3 C35 123.5(3) .
C46 N3 C47 118.8(3) .
O6 C35 N3 121.9(4) .
O6 C35 C36 120.9(4) .
N3 C35 C36 117.2(4) .
C37 C36 C35 119.4(4) .
C37 C36 C41 120.1(4) .
C41 C36 C35 120.5(4) .
C36 C37 H37 119.9 .
C36 C37 C38 120.3(4) .
C38 C37 H37 119.9 .
C37 C38 H38 119.1 .
C39 C38 C37 121.7(4) .
C39 C38 H38 119.1 .
C38 C39 C40 118.7(3) .
C38 C39 C42 122.7(4) 3_575
C40 C39 C42 118.6(3) 3_575
C39 C40 C41 119.0(3) .
C39 C40 C42 122.3(3) .
C41 C40 C42 118.7(3) .
C36 C41 C40 120.2(3) .
C36 C41 C45 119.9(3) .
C45 C41 C40 119.9(4) .
C40 C42 C39 119.1(3) 3_575
C43 C42 C39 121.5(4) 3_575
C43 C42 C40 119.3(3) .
C42 C43 H43 119.4 .
C42 C43 C44 121.1(4) .
C44 C43 H43 119.4 .
C43 C44 H44 119.6 .
C45 C44 C43 120.8(4) .
C45 C44 H44 119.6 .
C41 C45 C46 120.0(4) .
C44 C45 C41 120.0(4) .
C44 C45 C46 119.9(4) .
O5 C46 N3 121.4(4) .
O5 C46 C45 121.1(4) .
N3 C46 C45 117.5(4) .
N3 C47 H47 106.5 .
N3 C47 C48 111.9(3) .
N3 C47 C50 111.0(3) .
C48 C47 H47 106.5 .
C48 C47 C50 113.8(3) .
C50 C47 H47 106.5 .
C47 C48 H48A 108.7 .
C47 C48 H48B 108.7 .
H48A C48 H48B 107.6 .
C49 C48 C47 114.1(4) .
C49 C48 H48A 108.7 .
C49 C48 H48B 108.7 .
C48 C49 H49A 109.5 .
C48 C49 H49B 109.5 .
C48 C49 H49C 109.5 .
H49A C49 H49B 109.5 .
H49A C49 H49C 109.5 .
H49B C49 H49C 109.5 .
C47 C50 H50A 109.4 .
C47 C50 H50B 109.4 .
H50A C50 H50B 108.0 .
C51 C50 C47 111.4(4) .
C51 C50 H50A 109.4 .
C51 C50 H50B 109.4 .
C50 C51 H51A 109.5 .
C50 C51 H51B 109.5 .
C50 C51 H51C 109.5 .
H51A C51 H51B 109.5 .
H51A C51 H51C 109.5 .
H51B C51 H51C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O7 C63 1.235(5) .
O8 C52 1.230(5) .
N4 C52 1.399(6) .
N4 C63 1.391(6) .
N4 C64 1.494(6) .
C52 C53 1.477(7) .
C53 C54 1.370(6) .
C53 C58 1.402(6) .
C54 H54 0.9500 .
C54 C55 1.392(6) .
C55 H55 0.9500 .
C55 C56 1.390(6) .
C56 C57 1.429(6) .
C56 C59 1.462(6) 3_565
C57 C58 1.426(6) .
C57 C59 1.424(6) .
C58 C62 1.414(6) .
C59 C56 1.462(6) 3_565
C59 C60 1.391(6) .
C60 H60 0.9500 .
C60 C61 1.388(6) .
C61 H61 0.9500 .
C61 C62 1.370(6) .
C62 C63 1.477(6) .
C64 C65 1.473(7) .
C64 C67 1.364(14) .
C64 C67A 1.489(14) .
C65 H65A 0.9900 .
C65 H65B 0.9900 .
C65 C66 1.398(7) .
C66 H66A 0.9800 .
C66 H66B 0.9800 .
C66 H66C 0.9800 .
C67 H67A 0.9900 .
C67 H67B 0.9900 .
C67 C68 1.431(16) .
C68 H68A 0.9800 .
C68 H68B 0.9800 .
C68 H68C 0.9800 .
C68 H68D 0.9800 .
C68 H68E 0.9800 .
C68 H68F 0.9800 .
C68 C67A 1.361(13) .
C67A H67C 0.9900 .
C67A H67D 0.9900 .
O1 C1 1.219(4) .
O2 C12 1.228(4) .
N1 C1 1.399(5) .
N1 C12 1.395(5) .
N1 C13 1.509(5) .
C1 C2 1.480(5) .
C2 C3 1.371(5) .
C2 C7 1.403(5) .
C3 H3 0.9500 .
C3 C4 1.392(5) .
C4 H4 0.9500 .
C4 C5 1.391(5) .
C5 C6 1.424(5) .
C5 C8 1.468(5) 3_666
C6 C7 1.422(5) .
C6 C8 1.430(5) .
C7 C11 1.418(5) .
C8 C5 1.468(5) 3_666
C8 C9 1.388(5) .
C9 H9 0.9500 .
C9 C10 1.400(5) .
C10 H10 0.9500 .
C10 C11 1.375(5) .
C11 C12 1.477(5) .
C13 H13 1.0000 .
C13 C14 1.538(5) .
C13 C16 1.524(5) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C14 C15 1.522(5) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 C17 1.521(5) .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
O3 C18 1.223(4) .
O4 C29 1.222(4) .
N2 C18 1.405(5) .
N2 C29 1.393(5) .
N2 C30 1.500(5) .
C18 C19 1.479(5) .
C19 C20 1.370(5) .
C19 C24 1.410(5) .
C20 H20 0.9500 .
C20 C21 1.395(5) .
C21 H21 0.9500 .
C21 C22 1.388(5) .
C22 C23 1.426(5) .
C22 C25 1.471(5) 3_676
C23 C24 1.429(5) .
C23 C25 1.424(5) .
C24 C28 1.406(5) .
C25 C22 1.471(5) 3_676
C25 C26 1.392(5) .
C26 H26 0.9500 .
C26 C27 1.394(5) .
C27 H27 0.9500 .
C27 C28 1.375(5) .
C28 C29 1.487(5) .
C30 H30 1.0000 .
C30 C31 1.518(5) .
C30 C33 1.527(5) .
C31 H31A 0.9900 .
C31 H31B 0.9900 .
C31 C32 1.527(5) .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C33 C34 1.527(6) .
C34 H34A 0.9800 .
C34 H34B 0.9800 .
C34 H34C 0.9800 .
O5 C46 1.224(5) .
O6 C35 1.219(5) .
N3 C35 1.399(5) .
N3 C46 1.392(5) .
N3 C47 1.502(5) .
C35 C36 1.489(5) .
C36 C37 1.375(5) .
C36 C41 1.402(5) .
C37 H37 0.9500 .
C37 C38 1.401(5) .
C38 H38 0.9500 .
C38 C39 1.386(5) .
C39 C40 1.425(5) .
C39 C42 1.478(5) 3_575
C40 C41 1.426(5) .
C40 C42 1.430(5) .
C41 C45 1.411(5) .
C42 C39 1.478(5) 3_575
C42 C43 1.390(5) .
C43 H43 0.9500 .
C43 C44 1.395(5) .
C44 H44 0.9500 .
C44 C45 1.375(6) .
C45 C46 1.483(6) .
C47 H47 1.0000 .
C47 C48 1.527(6) .
C47 C50 1.536(6) .
C48 H48A 0.9900 .
C48 H48B 0.9900 .
C48 C49 1.516(6) .
C49 H49A 0.9800 .
C49 H49B 0.9800 .
C49 H49C 0.9800 .
C50 H50A 0.9900 .
C50 H50B 0.9900 .
C50 C51 1.520(6) .
C51 H51A 0.9800 .
C51 H51B 0.9800 .
C51 H51C 0.9800 .
